Late to the party, but I'll add some thoughs:
We're "cold water" sailors (Maritimes, Labrador, Great Lakes) and at least as of now, I have no desire to go to the tropics. When I retire, my dream is a Greenland- Iceland- Faroes- Scotland kind of trip or maybe the NW passage (which may be ice free then
). Due to the differing weather conditions I've experienced, some things are pretty high on the list:
Radar (sailing in day after day of fog can really suck)
Heat (more of an issue than AC for obvious reasons- Even the northern Lakes get pretty cold in the Summer) We have a solid fuel fireplace but I lust after a Webasto hydronic system- mmmmm, heeeeaaatt!
A decent autopilot (our boat isn't set up for a windvane) so therefore batteries and charging systems are more of a concern
I've been kicking around the idea of FLS (forward looking sonar) but won't be going back to "icy-land" anytime soon so that's on hold.
I've been ambivalent about chartplotters but would consider them a "nice to have". Ill agree that paper can get bulky on a long cruise. I'll probably wind up getting one down the road. (probably still keep the paper though)
If the boat sinks under me I'd like to have an EPIRB and a liferaft (they all suck to varying degrees but what's the alternative?)
Harnesses, jacklines etc. Finding a corpsickle is no fun, you gotta stay on the boat.
So I'm sort of a middle of the roader when it comes to creature comforts, good foulies , a good heater and good books are enough for me. TV is anathema but CD's are nice.
Offshore, SSB/Ham is really useful (as well as inshore when you're in the middle of nowhere). In the really high latitudes (further than I've gone) SSB doesn't work well so someone might consider a satphone- I never had one.
GPS- good to have, don't rely on it (Damn it's convenient). I'd love a gyrocompass (Big $$$) Sperry has a ring laser gyro (no moving parts)that if someone could get the price down would be just the thing(Hint Hint Hint
)- Sperry gouges for everything they make as far as I can tell. I don't have a solution to this one but a good magnetic compass and a good variation chart worked for most (fine for us up to the low 60's N.)
So in the philosophy department, spend the money to minimize risk to the boat and crew, go light on the creature comforts.